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Why Dealing with Difficult Clients Isn’t Always Common Sense

What’s common these days doesn’t make a whole lot of sense.

“Common sense” is a misnomer - the same as “white chocolate”. It’s tempting to believe that what’s common makes sense, just as something with chocolate in the name would be derived primarily from cocoa. But white chocolate is mostly sugar and milk, and much of what’s common these days doesn’t make a whole lot of sense.

Nowhere do you see this more prominently than the boom of “influencer” entrepreneurs.

Using every social media growth hack in the book (the same ones they’ll share in their $997 mastermind group!), this new horde of business influencers shout their “wisdom” into the world, where CEO’s-in-Training soak it all in. Before long, many of these ideas, when picked up and applied by enough people, become the new normal.

This leads to bad ideas being shared loudly, and becoming widely adopted and poorly executed. And when these ideas fail to serve a struggling business owner, they’re left to believe that they are the one to blame, since the strategy “works for everyone else”.

This happens frequently with creative agencies and client communication strategies. Agency owners flock to online groups and exclusive masterminds to share their latest, most ingenious tactics to dealing with difficult clients.

Stand your ground.

Reference the contract.

Communicate clearly but don’t let them gain the upper hand.

Cut your losses and let them go.

Much of the advice is devoid of the most crucial element that can both calm a frantic client and gain you a long-term partnership: a bit of humanity.

It’s not hard to deal with a challenging client, the kind who’s in your inbox every day wanting an update, a faster timeline. But that “common sense” advice floating out there today just won’t work—and if it does, it won’t work for long.

To understand why this won’t solve your client problems, you have to understand where their anxiety is coming from.


Understanding Difficult Clients

Assuming you’ve briefed your client on expectations, given them a timeline, and practiced effective client communication, it’s time to get to the root of what’s actually going on.

Most of the time, people don’t just act erratic for no reason—and yes, your clients are people, above all else. People with real thoughts, emotions, and most importantly, goals.

If clients are being difficult now, and they weren’t acting this way when they initially hired you, something’s changed. And it’s your job as the agency/freelancer/vendor to figure out what happened.

Here’s how to proceed:

  • Get on the phone with your client so they can hear your voice and you can hear theirs. This humanizes the entire experience—bonus points for video.

  • Be upfront about why you’re calling, but do not be on the defensive. Something like, “it seems like there are some misunderstandings or worries in your communication, so I wanted to connect…”

  • Ask questions until you have an understanding of what’s happening. Do not argue their concerns after every question.

  • Close the call with your plan for addressing their concerns, or a promise to send them your plans that day after some consideration and discussion with your team.

Ask more questions than you think you need to. Repeat back what you’re understanding from them so they can correct you in what you’ve heard. And don’t hang up until you feel like you have clarity on the issue(s).


Set Clear Expectations Upfront by Being Unexpected

A lot of new agency owners or those working with clients often want to overpromise in order to secure the contract. But this is not effective.

Clients expect you to make grand claims, tell them you can meet their ridiculously unrealistic timeline, and then fall over backward to achieve it so they don’t get mad.

What’s not expected is telling them that their timeline is unrealistic for the quality they (and your team) is expecting. That their idea won’t work for their industry and here’s why. That their desired goals may not be the most effective indicator of success, and which ones are instead.

This concept is the target of many vital scenes in TVs and movies. In Netflix’s new CIA-based show The Recruit, Noah Centineo plays Owen, hired to work as a lawyer for the CIA right out of law school. What makes his character so intriguing (and effective) is his upfront confidence when dealing with field agents, higher ups in the CIA, and even the attorney general despite being painfully green to the job.

Instead of rolling over and doing as they say, he takes the opposite approach, declaring what he will do and why he’s doing it differently, even going against the instructions of powerful people. The response from other characters? They actually like him more for it, moving him up the ladder a bit faster than he’d even like.

But this isn’t just in fiction. In Francesca Gino’s book Rebel Talent, she highlights the titled phenomenon where you can actually stand out and be seen as authoritative by going against what is expected. This is best pointed out in a study she performed herself where she taught a class wearing a pencil skirt and a plain heel. Later, she taught the same class with different students and wore the same pencil skirt, but this time she opted for red converse sneakers instead of heels.

“At the end of each session that day, I asked the students to complete a short survey assessing my professional status and competence. For instance, I asked them to guess at my status within the school and how likely my research was to be featured in the Harvard Business Review. Interestingly, the students viewed me as having greater status when I wore the red shoes. They also thought my consulting rate was higher. All thanks to a pair of red sneakers.”

Now, the goal is to not make the client feel wrong and present yourself as being right.

The goal is to break the mold of their expectations with confidence. And once you’ve got their attention by being unexpected, back up your claims with a plan that’s right for them.


Show the Project Progress

Another area that creates challenges with clients is that of project progress. Sending daily progress reports isn’t quite the same thing as giving your clients access to visually see the full project’s status, what is completed, what’s still being worked on, and where they can chime in (AKA, what they actually want to know). We understood this at Basecamp when we gave users the ability to invite clients directly into projects.

Choose exactly what your clients can and cannot see inside Basecamp
Choose exactly what your clients can and cannot see inside Basecamp

While Basecamp projects can remain as private as you like, you’re always able to share work with a client to quell concerns and easily keep them updated. Because at the end of the day, most clients just want to make sure the work is getting done.

But what you also need to remember is that the updates they ask for are not always what they truly want.


Share Status Updates Out of Excitement, Not Obligation

And be a human about it, would you? Sending a “status report” at the end of each day does nothing to increase your client’s confidence that you’re doing good work. You don’t need a scheduled update if you want to update the client regularly.

Many clients have money on the line. They want to feel good about the work being in your hands. Some of them have never hired this job out before. But a boring, lifeless status report isn’t engaging. Instead, send updates their way when you’re excited.

Marketing company doing a branding project? Send over the funny fonts you found, along with the one you decided to go with.

Graphic design agency? Ship off a few designs for other clients along with the one you made for them. Treat it like a sneak peek, a behind-the-scenes look (that also serves to showcase your agencies other design talents for ongoing work).

App developer? Send a funny meme that depicts how difficult a certain section was to build (one that the client insisted they have) along with the progress you’ve made.

Just be a human. Laugh. Joke. Share the fun of your job and it will be contagious. And more importantly, they’ll also see you and your team as real people with real thoughts and feelings, and that alone can do wonders for their difficult demeanor.

It’s not rocket science. It just goes against what’s touted as common nowadays. Be a person. Care about what they need. Show them you care about their needs.


If you’re looking for a better, truly common sense way to improve your collaboration with clients, look no further than the all-new Basecamp. It’s the fastest, easiest way to bring calm to the chaos of working with external clients. Best of all, you only pay for employees…invite as many clients as you want to your projects for free. Get started today in just a few minutes (no credit card, no commitment).

Learn with Basecamp.

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